title: A straightforward synthetic entry to cleavamine-type indole alkaloids by a ring-closing metathesis-vinyl halide Heck cyclization strategy.
abstract: An indole-templated ring-closing metathesis has been used to create the central nine-membered ring of the cleavamine-type alkaloids. A subsequent intramolecular vinyl halide Heck reaction upon the resulting azacyclononene ring completes the assembly of the strained 1-azabicyclo[6.3.1]dodecane framework of the alkaloids. The usefulness of the approach is illustrated with the synthesis of (±)-cleavamine and (±)-dihydrocleavamine.
authors.affiliation: Laboratory of Organic Chemistry, Faculty of Pharmacy, University of Barcelona, Barcelona 08028, Spain. bennasar@ub.edu
authors.forename: M-Lluïsa
authors.initials: ML
authors.lastname: Bennasar
authors.forename: Daniel
authors.initials: D
authors.lastname: Solé
authors.forename: Ester
authors.initials: E
authors.lastname: Zulaica
authors.forename: Sandra
authors.initials: S
authors.lastname: Alonso
mesh_terms: D003500:Cyclization; D006219:Halogens / Q000737:chemistry*; D026121:Indole Alkaloids / Q000138:chemical synthesis*; D015394:Molecular Structure; D014753:Vinyl Compounds / Q000737:chemistry*
chemical_list: C558890:20R-dihydrocleavamine; D006219:Halogens; D026121:Indole Alkaloids; D014753:Vinyl Compounds; C558889:cleavamine